Ah the wonders of search engines… I was looking for something else and ran across one of the best, and most sympathetic and insightful, articles I’ve seen crossdressing in the mainstream media. It was written by a reporter for a gay magazine who went out en femme with a local crossdressers group. (A PDF version of the article shows the photos as well, but it’s a 3.8MB file—the story starts page 12.)

Our intrepid reporterThe reporter gives a blow-by-blow account of the steps needed to look femme (the guy was even willing to shave his goatee, arms and legs) and gets help with a makeover—although the poor dear did end up looking like one of those early photos we don’t show anyone.

He observes: “A successful transformation involves more than slapping on powder and lipstick, throwing on a dress, and talking in a falsetto. As a creative art form, cross-dressing can be as demanding and expressive as painting or sculpting, singing or acting.”

What’s more interesting is his reaction to going out en femme—even dealing with a shocked significant other. (“My partner, who had no idea what I’m up to, runs around the apartment with his hands over his face, “I’m dating a drag queen! I’m dating a drag queen!”)

He runs into someone he knows and cops out with the excuse that he’s researching a story. “Dolly is disappointed. She wants to exist for her own sake, not as background material for work.” But pretty soon his inner girl asserts herself. “Monitoring myself stops, and being her kicks in. What felt awkward and strange is swiftly becoming natural…as long as the walk isn’t too far…. Around me, [the other CDs] are dancing, posing for the camera, laughing, and talking: a group of friends out for an evening together; nothing more, nothing less.”

I especially liked his analysis of his experience:

I have theories on why cross-dressing boosts confidence and self-esteem. First, the learning and mastering of new skills. Putting on makeup, selecting the right clothes, preparing hair, nails, and undergarments, walking gracefully in heels, mastering vocal control, these are all challenging to the newcomer and, when competently executed, create a strong sense of satisfaction. A successful transformation involves more than slapping on powder and lipstick, throwing on a dress, and talking in a falsetto. As a creative art form, cross-dressing can be as demanding and expressive as painting or sculpting, singing or acting.

Secondly, as Jacilynn explained, cross-dressing draws out characteristics that often have been lying dormant. It was surprising how many mannerisms rose to the occasion without conscious effort. The way I held my drink, how I sat, even the way I smiled were all subtly, and not so subtly, adjusted to match my new look. Exercise is effective when you push the muscles past their comfort zone, causing them to grow to handle the increased demand. Personality and character, when pushed beyond their comfort zone, respond in much the same way, becoming stronger, more flexible, and resilient. When the clothes and cosmetics are removed, the strength remains.

Finally, overcoming any fear empowers people, and for many men, loss of masculinity carries some fearful misconceptions. Dressing up, going out, having a good time, and coming home feeling positive has diminished what fears I held about not being able to maintain a manly image. That shirt with the buttons on the wrong side no longer makes me anxious, and I suspect if I found an article of clothing made for a woman that looked great on me, I would buy it, wear it, and not think twice.

There is one more aspect of cross-dressing that is not innate to the practice, but which can be the most uplifting part. This may also be the easiest for gays and lesbians to understand. It is the joy of sharing and expressing parts of your sexuality and gender that extend out of what mainstream society would call the norm with others who accept and appreciate instead of judging or tolerating. Spending all that time and energy cultivating a look and nurturing your feminine or masculine qualities to new heights, only to sit in your living room, shades drawn, watching TV or dancing alone to the stereo does not produce the same elation as sharing the experience with friends, family, and lovers. It is a feeling not so different from loving another, but being too afraid of what people might think to share that love. This is why groups such as Masquerade and the work they do are a vital and necessary part of the glbt community, not only building that “t”in glbt, but also building stronger ties between the genders.

As I dismantle Dolly, removing hair and clothing, tearing away press-on nails and clip-on earrings, I understand why Vanessa framed the choice between herself and a potential partner the way she did. Watching the makeup run down the drain, a human being dissolves and washes away. Dolly was the physical manifestation of my feminine side that until now never had the chance to strut her stuff. Now that we’ve met, there is no way to banish her to those inner regions again. Two parts of my personality have been integrated in an inventive, gentle way, leaving me more whole, more complete, and better off. Knowing this, the question is no longer ‘why do some people cross-dress?’ The question is ‘why don’t more people cross-dress?’